2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->1)-2,3-O-isopropylidene-α-D-mannopyranoside | 1333473-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->1)-2,3-O-isopropylidene-α-D-mannopyranoside
• CAS: 1333473-93-0
• 化学式: C₄₃H₅₀O₁₁
• 分子量: 742.863
• InChiKey: XCWFYCRCJFCNTK-FXWZYTRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  54.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  123.53
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->1)-2,3-O-isopropylidene-α-D-mannopyranoside 在 4-二甲氨基吡啶 、 甲酸 、 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 苯 为溶剂， 反应 21.0h， 生成 β-D-glucopyranosyl-(1->1)-6-O-palmitoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis, gp120 binding and anti-HIV activity of fatty acid esters of 1,1-linked disaccharides

  摘要：

  Inspired by the anti-human immunodeficiency virus (HIV) activity of analogues of beta-galactosylceramide (GalCer), a set of mono- and di-saccharide fatty acid esters were designed as GalCer mimetics and their binding to the V3 loop peptide of HIV-1 and anti-HIV activity evaluated. 1,1-linked Gal-Man and Glu-Man disaccharides with an ester on the Man subunit bound the V3 loop peptide and inhibited HIV infectivity in single round infection assays with the TZM-bl cell line. IC50's were in the 50 mu M range with no toxicity to the cells at concentrations up to 200 mu M. These compounds appear to inhibit virus entry at early steps in viral infection since they were inactive if added post viral entry. Although these compounds were found to bind to the V3 loop peptide of gp120, it is not clear that this interaction is responsible for their anti-HIV activity because the relative binding affinity of closely related analogues did not correlate with their antiviral behavior. The low cytotoxicity of these 1,1-linked disaccharide fatty acid esters, combined with the easy accessibility to structurally diverse analogues make these molecules attractive leads for new topical anti-viral agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.078
• 作为产物：
  描述：

  phenyl 2,3:4,6-bis-O-isopropylidene-1-thio-α-D-mannopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 1.5h， 生成 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->1)-2,3-O-isopropylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis, gp120 binding and anti-HIV activity of fatty acid esters of 1,1-linked disaccharides

  摘要：

  Inspired by the anti-human immunodeficiency virus (HIV) activity of analogues of beta-galactosylceramide (GalCer), a set of mono- and di-saccharide fatty acid esters were designed as GalCer mimetics and their binding to the V3 loop peptide of HIV-1 and anti-HIV activity evaluated. 1,1-linked Gal-Man and Glu-Man disaccharides with an ester on the Man subunit bound the V3 loop peptide and inhibited HIV infectivity in single round infection assays with the TZM-bl cell line. IC50's were in the 50 mu M range with no toxicity to the cells at concentrations up to 200 mu M. These compounds appear to inhibit virus entry at early steps in viral infection since they were inactive if added post viral entry. Although these compounds were found to bind to the V3 loop peptide of gp120, it is not clear that this interaction is responsible for their anti-HIV activity because the relative binding affinity of closely related analogues did not correlate with their antiviral behavior. The low cytotoxicity of these 1,1-linked disaccharide fatty acid esters, combined with the easy accessibility to structurally diverse analogues make these molecules attractive leads for new topical anti-viral agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.078